(Z)-N-benzyl-N-(3-trimethylsilylprop-2-ynyl)-3-(phenylseleno)acrylamide | 1042929-56-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (Z)-N-benzyl-N-(3-trimethylsilylprop-2-ynyl)-3-(phenylseleno)acrylamide
• 英文别名: (Z)-N-benzyl-3-phenylselanyl-N-(3-trimethylsilylprop-2-ynyl)prop-2-enamide
• CAS: 1042929-56-5
• 化学式: C₂₂H₂₅NOSeSi
• 分子量: 426.492
• InChiKey: GOBPWAZDYUGBGJ-ICFOKQHNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.44
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (Z)-N-benzyl-N-(3-trimethylsilylprop-2-ynyl)-3-(phenylseleno)acrylamide 在 四(三苯基膦)铂 作用下， 以 甲苯 为溶剂， 反应 3.5h， 生成 (E)-1-benzyl-5-[1-(phenylseleno)trimethylsilylmethylene]-5,6-dihydro-1H-pyridin-2-one 、 (Z)-1-benzyl-5-[1-(phenylseleno)trimethylsilylmethylene]-5,6-dihydro-1H-pyridin-2-one
  参考文献：
  名称：

  Platinum-Catalyzed Intramolecular Vinylchalcogenation of Alkynes with β-Phenylchalcogeno Conjugated Amides

  摘要：

  Platinum-catalyzed intramolecular vinylthiolation and -selenation of internal alkynes with vinylchalcogenides 1 having a carbamoyl group on cis-beta-position of vinyl moiety was developed. The conjugated six-membered lactam framework 2 was constructed in 1 high yields. Density functional theory calculations for alkyne insertion processes suggest seven-membered platinacycle 3 is a kinetically favored intermediate of this catalytic system.

  DOI：

  10.1021/ja804121j
• 作为产物：
  描述：

  (Z)-3-(phenylseleno)acryloyl chloride 、 6,6-二甲基-1-苯基-2-氮杂-6-硅杂-4-庚炔 在 sodium carbonate 作用下， 以 二氯甲烷 为溶剂， 生成 (Z)-N-benzyl-N-(3-trimethylsilylprop-2-ynyl)-3-(phenylseleno)acrylamide
  参考文献：
  名称：

  Platinum-Catalyzed Intramolecular Vinylchalcogenation of Alkynes with β-Phenylchalcogeno Conjugated Amides

  摘要：

  Platinum-catalyzed intramolecular vinylthiolation and -selenation of internal alkynes with vinylchalcogenides 1 having a carbamoyl group on cis-beta-position of vinyl moiety was developed. The conjugated six-membered lactam framework 2 was constructed in 1 high yields. Density functional theory calculations for alkyne insertion processes suggest seven-membered platinacycle 3 is a kinetically favored intermediate of this catalytic system.

  DOI：

  10.1021/ja804121j

文献信息

• Platinum-Catalyzed Intramolecular Vinylchalcogenation of Alkynes with β-Phenylchalcogeno Conjugated Amides
  作者：Masashi Toyofuku、Shin-ichi Fujiwara、Tsutomu Shin-ike、Hitoshi Kuniyasu、Nobuaki Kambe

  DOI：10.1021/ja804121j

  日期：2008.8.13

  Platinum-catalyzed intramolecular vinylthiolation and -selenation of internal alkynes with vinylchalcogenides 1 having a carbamoyl group on cis-beta-position of vinyl moiety was developed. The conjugated six-membered lactam framework 2 was constructed in 1 high yields. Density functional theory calculations for alkyne insertion processes suggest seven-membered platinacycle 3 is a kinetically favored intermediate of this catalytic system.